Sodium Hydroxide → 2-Amino-4-methyl-thiazole-5-carboxylic acid

HRID 45308

Reaction equation

HRID 45308 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=[O:9])=[C:5]([CH3:7])[N:6]=1.[OH-].[Na+]>O1CCCC1.O>[NH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.5 mmol) and NaOH (5.40 g, 135.00 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed by evaporation, and the residue was neutralized with 5% hydrochloric acid solution to pH 5˜6. The precipitate obtained was collected by filtration and dried to afford 2-amino-4-methylthiazole-5-carboxylic acid (5.20 g, 94%); 1H NMR (DMSO-d6, 300 MHz) δ 7.63 (s, 2H), 2.30 (s, 3H). MS (ES+) m/z 159.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customTetrahydrofuran was removed by evaporation
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-80b00884331e40f7ae8f1fced1fd8601
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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